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CA2526586A1 - The use of fumaric acid derivatives for treating cardiac insufficiency, and asthma - Google Patents

The use of fumaric acid derivatives for treating cardiac insufficiency, and asthma Download PDF

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Publication number
CA2526586A1
CA2526586A1 CA002526586A CA2526586A CA2526586A1 CA 2526586 A1 CA2526586 A1 CA 2526586A1 CA 002526586 A CA002526586 A CA 002526586A CA 2526586 A CA2526586 A CA 2526586A CA 2526586 A1 CA2526586 A1 CA 2526586A1
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Canada
Prior art keywords
fumaric acid
fumarates
monoalkyl
monoamido
use according
Prior art date
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Granted
Application number
CA002526586A
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French (fr)
Other versions
CA2526586C (en
Inventor
Rajendra Kumar Joshi
Hans-Peter Strebel
Christian Zaugg
Michael Tamm
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Biogen International GmbH
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Individual
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Priority claimed from DE10360869A external-priority patent/DE10360869A1/en
Application filed by Individual filed Critical Individual
Publication of CA2526586A1 publication Critical patent/CA2526586A1/en
Application granted granted Critical
Publication of CA2526586C publication Critical patent/CA2526586C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/225—Polycarboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
    • A61K31/231—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms having one or two double bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
    • A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

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  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Emergency Medicine (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pulmonology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Vascular Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Saccharide Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

According to a first aspect the invention relates to the use of fumaric acid derivatives selected from the group consisting of dialkyl fumarates, monoalk yl hydrogen fumarates, fumaric acid monoalkyl ester salts, fumaric acid monoamides, monoamido fumaric acid salts, fumaric acid diamides, monoalkyl monoamido fumarates, carbocyclic and oxacarbocyclic oligomers of these compounds and mixtures thereof for preparing a drug for the treatment or prevention of cardiac insufficiency, in particular left ventricular insufficiency, myocardial infarction and angina pectoris. According to a second aspect the invention relates to the use of fumaric acid derivatives, selected from the group consisting of dialkyl fumarates, monoalkyl hydrogen fumarates, fumaric acid monoaklyl ester salts, fumaric acid monoamido fumari c acid salts, fumaric acid diamides, monoalkyl monoamido fumarates, carbocycli c and oxacarbocyclic oligomers of these compounds and mixtures thereof for preparing a drug for the treatment of asthma and chronic obstructive pulmona ry diseases, especially asthma caused by allergies, infections, analgesics, job conditions or physical effort, mixed forms of asthma, or asthma cardiale.</S DOAB>

Claims (26)

1. The use of fumaric acid derivatives selected from the group consisting of dialkyl fumarates, monoalkyl hydrogen fumarates, fumaric acid monoalkyl ester salts, fumaric acid monoamides, monoamido fumaric acid salts, fumaric acid diamides, monoalkyl monoamido fumarates, carbocyclic and oxacarbocyclic oligomers of these compounds and mixtures of the foregoing for preparing a drug for the treatment or prevention. of cardiac insufficiency, particularly left ventricular insufficiency, myocardial infarct and angina pectoris.
2.. The use of fumaric acid derivatives selected from the group consisting of dialkyl fumarates, monoalkyl hydrogen fumarates, fumaric acid monoalkyl ester salts, fumaric acid monoamides, monoamido fumaric acid salts, fumaric acid diamides, monoalkyl monoamido fumarates, carbocyclic and oxacarbocyclic oligomers of these compounds and mixtures of the foregoing for preparing a drug for the treatment of asthma and chronic obstructive pulmonary diseases in general, especially asthma caused by allergies, infections, analgesics, job conditions or physical effort, mixed forms of asthma, or asthma cardiale.
3. The use according to claim 2 in combination with a glucocorticoid, preferably selected from the group consisting of dexamethasone, cortisone, hydrocortisone, prednisolone, prednisone, methylprednisolone, fluocortolone, triamcinolone, beclomethasone, budenoside, flunisonide, fluticasone, betamethasone, and pharmaceutically acceptable salts and derivatives thereof.
4. The use according to claim 1, 2 or 3 wherein the fumaric acid derivative is selected from one or more fumaric acid dialkyl esters of the formula I

wherein R1 and R2 which may be the same or different independently represent a linear, branched or cyclic, saturated or unsaturated C1-24 alkyl radical or a aryl radical and wherein said radicals may optionally be substituted with halogen (F, Cl; Br, I), hydroxy, C1 - 4 alkoxy, C1-4-alkyl, nitro or cyano.
5. The use according to claim 1, 2 or 3 wherein the fumaric acid derivative is selected from one or more fumaric acid monoalkyl esters of the formula II

wherein - R1 represents a linear, branched or cyclic, saturated or unsaturated C1-24 alkyl radical or a C5 - 20 aryl radical;
- A represents hydrogen, an alkaline or alkaline earth metal cation or a physiologically acceptable transition metal canon, preferably selected from Li+, Na+, K+, Mg2+, Ca2+, Zn2+, Fe2+, and Mn2+, and - n equals 1 or 2 and corresponds to the valence of A.
6. The use according to any of the previous claims wherein the fumaric acid derivative is selected from one or more compounds of the formulae (I) and (II) and mixtures thereof.
7. The use according to claim 6 wherein the fumaric acid derivative is selected from the group consisting of fumaric acid dimethyl ester, fumaric acid diethyl ester, fumaric acid methyl ethyl ester, methyl hydrogen fumarate, ethyl hydrogen fumarate, calcium methyl fumarate, calcium ethyl fumarate, magnesium methyl fumarate, magnesium ethyl fumarate, zinc methyl fumarate, zinc ethyl fumarate, iron methyl fumarate, iron ethyl fumarate and mixtures thereof.
8. The use according to claim 1, 2, or 3 wherein the fumaric acid derivative is selected from one or more fumaric acid amides of the general formula III

wherein R a represents OR3 or a D- or L-amino acid radical -NH-CHR4-COOH bonded via an amide bond, wherein R3 is hydrogen, a straight-chain or branched, optionally substituted C1 - 24 alkyl radical, a phenyl radical or a C6 - 10 aralkyl radical and R4 is a side chain of a natural or synthetic amino acid;
and R b represents a D- or L-amino acid radical -NH-CHR5-COOH bonded via an amide bond, wherein R5 is a side chain of a natural or synthetic amino acid which may be the same as or different from R4, or a peptide radical with 2 to 100 amino acids bonded via an amide bond, which amino acids may be the same or different.
9. The use according to claim 8, wherein the side chain of a natural or synthetic amino acid is selected from the group consisting of the side chains of Ala, Val, Leu, Ile, Trp, Phe, Met, Tyr, Thr, Cys, Asn, Gln, Asp, Glu, Lys, Arg, His, Citrulline, Hcy, Hse, Hyp, Hyl, Orn, Sar, and Me-Gly, preferably Gly, Ala, Val, Ile, Leu, and Me-Gly.
10. The use according to claim 8 wherein R a is the radical -OR3 and R b is an L-amino acid radical -NH-CHR5-COOH or a peptide radical, R5 being as defined in claim 8.
11. The use according to claim 1, 2, or 3 wherein the fumaric acid derivative is a carbocyclic oligomer consisting of 2 to 10 fumaric acid moieties as repetitive moieties, wherein the fumaric acid moieties are derived from monomers selected from the group consisting of fumaric acid, dialkyl fumarates, monoalkyl hydrogen fumarates, fumaric acid monoamides, fumaric acid diamides, monoalkyl monoamido fumarates and salts and mixtures thereof.
12. The use according to any of the previous claims wherein the alkyl radicals having 1 to 24 carbon atoms are selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, t-butyl, pentyl, cyclopentyl, 2-ethyl hexyl;
hexyl, cyclohexyl, heptyl, cycloheptyl, octyl, vinyl, allyl, 2-hydroxy ethyl, 2 or 3 hydroxy propyl, 2,3-dihydroxypropyl, 2-methoxy ethyl, methoxy methyl, 2-methoxy propyl, 3-methoxy propyl or 2,3-dimethoxy propyl, preferably methyl or ethyl.
13. The use according to any of the previous claims wherein the drug is provided in a form suitable for oral, rectal, transdermal, dermal, ophthalmological, nasal, pulmonary or parenteral application.
14. The use according to claim 13 wherein the drug is provided in the form of tablets, coated tablets, capsules, granulate, solutions for drinking, liposomes, nano-particles; nano-capsules, micro-capsules, micro-tablets, pellets or powders and in the form of granules filled in capsules or sachets, micro-tablets filled in capsules or sachets, pellets filled in capsules or sachets, nano-particles filled in capsules or sachets or powder filled in capsules or sachets.
15. The use according to.claim 14, wherein the drug is present in the form of nano-particles, pellets or micro-tablets which may optionally be filled in sachets or capsules.
16. The use according to any of the claims 14 to 15 wherein the solid oral dosage forms are provided with an enteric coating.
17. The use according to any of the previous claims wherein the drug contains an amount of fumaric acid 'derivative(s) corresponding to 1 to 500 mg of fumaric acid.
18. A method of inhibiting PDGF induced thymidine uptake of bronchial smooth muscle cells, which method includes the step of cultivating the cells in presence of an amount of a fumaric acid derivative sufficient to inhibit said uptake, which fumaric acid derivative is selected from the group consisting of dialkyl fumarates, monoalkyl hydrogen fumarates, fumaric acid monoalkyl ester salts, fumaric acid monoamides, monoamido fumaric acid salts, fumaric acid diamides, monoalkyl monoamido fumarates, carbocyclic and oxacarbocyclic oligomers of these compounds and mixtures of the foregoing.
19. A method of inhibiting bronchial smooth muscle cell proliferation, which method includes the step of bringing bronchial smooth muscle cells directly or indirectly in contact with a proliferation inhibiting amount of a fumaric acid derivative selected from the group consisting of dialkyl fumarates, monoalkyl hydrogen fumarates, fumaric acid monoalkyl ester salts, fumaric acid monoamides, monoamido fumaric acid salts, fumaric acid diamides, monoalkyl monoamido fumarates, carbocyclic and oxacarbocyclic oligomers of these compounds and mixtures of the foregoing.
20. The method of claim 18 or 19, wherein the fumaric acid derivative is selected from one or more fumaric acid dialkyl esters of the formula I

wherein R1 and R2 which may be the same or different independently represent a linear, branched or cyclic, saturated or unsaturated C1 - 24 alkyl radical or a C5 - 20 aryl radical and wherein said radicals may optionally be substituted with halogen (F, Cl, Br, I), hydroxy, C1-4 alkoxy, C1-4-alkyl, nitro or cyano.
21. The method of claim 18 or 19, wherein the fumaric acid derivative is selected from one or more fumaric acid monoalkyl esters of the formula II

wherein R1 represents a linear, branched or cyclic, saturated or unsaturated C1-24 alkyl radical or a C5 - 20 aryl radical;

- A represents hydrogen, an alkaline or alkaline earth metal cation or a physiologically acceptable transition metal cation, preferably selected from Li+, Na+, K+, Mg2+, Ca2+, Zn2+, Fe2+, and Mn2+, and - n equals 1 or 2 and corresponds to the valence of A.
22. The method of any of claims 21 or 22, wherein the fumaric acid derivative is selected from one or more compounds of the formulae (I) and (II) and mixtures thereof.
23. The method of claim 19, which is carried out in vivo, by administering the fumaric acid derivative to a subject.
24. The method of claim 23, wherein said administration is an oral administration.
25. The use of a fumaric acid derivative selected from the group consisting of dialkyl fumarates, monoalkyl hydrogen fumarates, fumaric acid monoalkyl ester salts, fumaric acid monoamides, monoamido fumaric acid salts, fumaric acid diamides, monoalkyl monoamido fumarates, carbocyclic and oxacarbocyclic oligomers of these compounds and mixtures of the foregoing, for inhibiting bronchial smooth muscle cell proliferation.
26. The use of a fumaric acid derivative selected from the group consisting of dialkyl fumarates, monoalkyl hydrogen fumarates, fumaric acid monoalkyl ester salts, fumaric acid monoamides, monoamido fumaric acid salts, fumaric acid diamides, monoalkyl monoamido fumarates, carbocyclic and oxacarbocyclic oligomers of these compounds and mixtures of the foregoing, for inhibiting PDGF induced STAT1 activation.
CA2526586A 2003-09-09 2004-09-03 The use of fumaric acid derivatives for treating cardiac insufficiency, and asthma Expired - Fee Related CA2526586C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE10341530 2003-09-09
DE10341530.0 2003-09-09
DE10360869.9 2003-12-23
DE10360869A DE10360869A1 (en) 2003-09-09 2003-12-23 Use of fumaric acid derivatives for the treatment of heart failure, hyperkeratosis and asthma
PCT/EP2004/009835 WO2005023241A1 (en) 2003-09-09 2004-09-03 The use of fumaric acid derivatives for treating cardiac insufficiency, and asthma

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CA2526586A1 true CA2526586A1 (en) 2005-03-17
CA2526586C CA2526586C (en) 2010-03-16

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US (3) US20070027076A1 (en)
EP (2) EP1913942B1 (en)
AT (1) ATE380027T1 (en)
AU (1) AU2004269903B2 (en)
BR (1) BRPI0410805A (en)
CA (1) CA2526586C (en)
DE (1) DE602004010531T2 (en)
DK (1) DK1663197T3 (en)
ES (1) ES2297461T3 (en)
MX (1) MXPA06002657A (en)
NO (1) NO335991B1 (en)
PL (1) PL1663197T3 (en)
RU (1) RU2313339C2 (en)
SI (1) SI1663197T1 (en)
WO (1) WO2005023241A1 (en)

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